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Literature summary for 4.1.3.3 extracted from

  • Woodhall, T.; Wiliams, G.; Berry, A.; Nelson, A.
    Creation of a tailored aldolase for the parallel synthesis of sialic acid mimetics (2005), Angew. Chem., 44, 2109-2112.
    View publication on PubMed
Search for more literature for 4.1.3.3

Protein Variants

Protein Variants Comment Organism
E192N the turnover-number for sialic acid is 65% of the wild-type value, the Km-value for sialic acid is 8.6fold higher than the wild-type value, the turnover-number for (2R,3R,4R)-6-[(aminooxy)carbonyl]-3,4,6-trihydroxy-N-propyltetrahydro-2H-pyran-2-carboxamide is 57% of the wild-type value, the KM-value for (2R,3R,4R)-6-[(aminooxy)carbonyl]-3,4,6-trihydroxy-N-propyltetrahydro-2H-pyran-2-carboxamide is 28.2fold lower than the wild-type value. The mutant enzyme is most efficient in catalysis of the synthesis of the tertiary amides (4S,5R,6R)-6-[(diethylamino)carbonyl]-2,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylic acid, (4R,5R,6R)-6-[(diethylamino)carbonyl]-2,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylic acid, (4S,5R,6R)-2,4,5-trihydroxy-6-{[methyl(propyl)amino]carbonyl}tetrahydro-2H-pyran-2-carboxylic acid, (4R,5R,6R)-2,4,5-trihydroxy-6-{[methyl(propyl)amino]carbonyl}tetrahydro-2H-pyran-2-carboxylic acid, (4S,5R,6R)-6-[(dipropylamino)carbonyl]-2,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylic acid, (4R,5R,6R)-6-[(dipropylamino)carbonyl]-2,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylic acid, (4S,5R,6R)-6-[(dibutylamino)carbonyl]-2,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylic acid, (4R,5R,6R)-6-[(dibutylamino)carbonyl]-2,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylic acid, (4S,5R,6R)-2,4,5-trihydroxy-6-(pyrrolidin-1-ylcarbonyl)tetrahydro-2H-pyran-2-carboxylic acid, (4R,5R,6R)-2,4,5-trihydroxy-6-(pyrrolidin-1-ylcarbonyl)tetrahydro-2H-pyran-2-carboxylic acid, (4S,5R,6R)-2,4,5-trihydroxy-6-(piperidin-1-ylcarbonyl)tetrahydro-2H-pyran-2-carboxylic acid, (4R,5R,6R)-2,4,5-trihydroxy-6-(piperidin-1-ylcarbonyl)tetrahydro-2H-pyran-2-carboxylic acid, (4S,5R,6R)-2,4,5-trihydroxy-6-(morpholin-4-ylcarbonyl)tetrahydro-2H-pyran-2-carboxylic acid, (4R,5R,6R)-2,4,5-trihydroxy-6-(morpholin-4-ylcarbonyl)tetrahydro-2H-pyran-2-carboxylic acid Haemophilus influenzae

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.39
-
 (2R,3R,4R)-6-[(aminooxy)carbonyl]-3,4,6-trihydroxy-N-propyltetrahydro-2H-pyran-2-carboxamide mutant enzyme E192N Haemophilus influenzae
4.4
-
 sialic acid wild-type enzyme Haemophilus influenzae
11
-
 (2R,3R,4R)-6-[(aminooxy)carbonyl]-3,4,6-trihydroxy-N-propyltetrahydro-2H-pyran-2-carboxamide wild-type enzyme Haemophilus influenzae
38
-
 sialic acid mutant enzyme E192N Haemophilus influenzae

Organism

Organism UniProt Comment Textmining
Haemophilus influenzae
-
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
(2R,3R,4R)-6-[(aminooxy)carbonyl]-3,4,6-trihydroxy-N-propyltetrahydro-2H-pyran-2-carboxamide
-
 Haemophilus influenzae ?
-
 ?
N-Acetylneuraminic acid
-
 Haemophilus influenzae N-Acetyl-D-mannosamine + pyruvate
-
 ?

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
0.057 0.65 (2R,3R,4R)-6-[(aminooxy)carbonyl]-3,4,6-trihydroxy-N-propyltetrahydro-2H-pyran-2-carboxamide mutant enzyme E192N Haemophilus influenzae
1.23
-
 (2R,3R,4R)-6-[(aminooxy)carbonyl]-3,4,6-trihydroxy-N-propyltetrahydro-2H-pyran-2-carboxamide wild-type enzyme Haemophilus influenzae
2.833
-
 sialic acid mutant enzyme E192N Haemophilus influenzae
3 6 sialic acid mutant enzyme E192N Haemophilus influenzae
4.33
-
 sialic acid wild-type enzyme Haemophilus influenzae
10.83
-
 (2R,3R,4R)-6-[(aminooxy)carbonyl]-3,4,6-trihydroxy-N-propyltetrahydro-2H-pyran-2-carboxamide mutant enzyme E192N Haemophilus influenzae